Holiday home rentals in Western Massachusetts

La Maison Hudson: Charming 1BR In Prime Location

Welcome to La Maison in Hudson! This charming three-story townhouse, just two blocks from vibrant Warren Street, is perfect for families, friends, or a romantic getaway. Apartment 2 offers 1 bedroom, 1 bath, and accommodates 2 guests. Enjoy cozy thrifted decor, a private balcony, convenient parking, and a fully equipped kitchen with a dining table for six. Warren St: 3-min walk Train station: 15-min walk Olana: 8-min drive Art OMI: 15-min drive Your ideal mix of convenience & culture awaits!

Lakefront Retreat | Kayaks, Paddle Board & Hot tub

Welcome to the newly renovated lakefront vacation house in the Catskills. It is perfect for family & friends looking for a getaway in the Hudson valley and Catskill mountains. Close to ski resorts like Hunter & Windham. This peaceful retreat is located in a beautiful lake community with a large waterfront backyard.  You will enjoy:  • Gathering around the fire pit by the waterfront with s’mores • Relaxing in the Hot Tub overlooking the lake • Wake up to the beautiful lake view from your bedroom

Spacious Urban APT w/4BR & Office in Albany

Visiting Albany for work, vacation, or to visit family? The Twitchell Estate is a spacious 4BR home that will be perfect for your stay. This elegantly designed Boho Chic rental comes with amenities such as self-check-in, Netflix, Disney+, Apple TV, and many other streaming options if you're looking to relax indoors, and a private laptop-friendly office with Wi-Fi if you need to get work done. Enjoy free coffee and tea in the stocked kitchen, with everything you need to feel like you are at home.

Private new house on 10 acres of pristine nature

Brand new home! Bring friends and family to this private and stylish place. House provides everything you need for a comfortable and peaceful stay. Fully equipped kitchen, inviting living spaces, large front and back yards with many exploring trails and a pond a few steps away from the house. Close to many 5 star restaurants, wineries, galleries and shops. Hiking, swimming, boating, skiing just to mention a few outdoor activities Close by: Kent School Mohawk Ski Area Lake Waramug High Watch

The Lake

Welcome to Lake Congamond's North Pond! Wake up every day just steps from the water. Grill out on the brand new Trex deck with stunning water views, and dock your boats for the duration of your stay. This home features ample parking, central air, cornhole boards, an outdoor dartboard, and a propane-fueled fire pit. The location is great as the house is just minutes away from Bars, Restaurants, and Golf Courses. This vacation rental truly has it all! Book your stay today!

Winterberry Lodge: Newly Renovated at Jiminy Peak

NEWLY RENOVATED - 3 BR 2 BA~ sleeps 10, swimming pool, private deck w/ awning, Weber grill Multi-level 3 bedroom house only 2 miles from Jiminy Peak (has community pool). Fully equipped RENOVATED kitchen, fully renovated bathrooms, new floors and carpeting, has "perfect hill" right off the deck to sled and a Weber grill for warmer weather. Cozy loft area to enjoy board games and several smart TVs throughout . Wonderful base to enjoy the Berkshires year around!

Perfect Serene Waterfront All Season Retreat!

Enjoy everything the Berkshires has to offer from this beautiful, secluded, nicely renovated waterfront house set on two wooded acres of forested land. Explore the stream that runs through the property, or just sit on the large deck or down by the crystal clear lake and listen to the sounds of nature while feeling the warm sun on your face. Very private--just one near neighbor. The sunny house has 2 bedrooms, study with sofa bed, 2 full baths, full kitchen!

Mountain escape in Hunter/Tannersville

Nestled between Hunter and Tannersville, our cozy house is 5 minutes from Hunter Mountain and hiking trails. Enjoy skiing, snowboarding, hiking, lakes, zip-lining, and more. Nearby are great restaurants, boutique stores, theaters, a supermarket, and more. Our home has four spacious bedrooms, two bathrooms, a full kitchen, and a living area for entertaining. Enjoy ping-pong, the outdoor hot tub, or gather around the fire pit for a mountain bonfire!

Riverfront rustic farmhouse near Rhinebeck

This historic Clinton Hollow house was built by Isaac Fraleigh in the late 1700's and overlooks the waterfalls of Wappingers Creek. The house has the architectural details of an antique colonial and the open, spacious feel of a modern contemporary. The great room with its big fireplace has different vibes and seating areas and is just perfect for family and friends gathering. The Petanque field in the garden add a fun convivial activity.

Chez Moo - Hot Tub with a View

Less than 45 minute to multiple ski spots! Beautiful home with spectacular Eastern view of Western Vermont mountains. Large, brand new hot tub that fits 7 people. Billiards room. While being beautifully secluded, there is quick and easy access to Battenkill Creamery and Farm Store, R.S. Taylor and Sons Brewery, and Hick's Orchard to name a few. Please note: there is a large TV on the lower level across from the pool table.

Home in Great Barrington. Steps from downtown!

Central and Private! Just steps away from historic downtown Great Barrington. East Mountain Hiking trails are a quick walk away. Enjoy sunset views with friends and family, before you walk into town for a night out! Butternut Ski Area: 5-10 min drive(traffic depending) Tanglewood: 20-25 min This new home features all new appliances and furniture. Enjoy luxury, charm, and privacy while you rest easy at The Maple. 🫶

Explore the Berkshires from this charming home.

The whole group will enjoy easy access to everything from this centrally located place. Ski Bousquet, Butternut, or Jiminy Peak. Visit charming towns of Great Barrington, Lee, Stockbridge, Lenox, Adams, N. Adams and Williamsburg. All within a short drive. Soak up some culture by visiting Clark Museum, Mass Moca, or the Rockwell Museum, or listen to some great live music at Tanglewood during the summers.